At the end of the last ice age, about 11,000 years ago, the present-day Connecticut River came into existence. Since that time humans have lived along its shores. The first people to inhabit the Connecticut River Valley were Native Americans who hunted caribou, wooly mammoth, and other cold-adapted animals. Native American populations flourished in the valley as the climate became progressively milder and more temperate.

In 1614, the first Europeans entered the Connecticut River estuary and by the 1630s fur trading posts extended into Massachusetts. In the following century, English colonists moved farther and farther up river into Vermont and New Hampshire, displacing the Native Americans. The Valley area grew rapidly as a major transportation route to the north, a manufacturing area and an important agricultural zone. In addition to its commercial sucess, the area has a large number of colleges and universities.

The western shore of the river is the gateway to the Berkshire Mountains in western Massachusetts and is the most heavily populated area covered by the Select Berkshire Inns web site. The cities of Greenfield, in the north, Northhampton in the center and the Springfield area in the south are the main points of entry from Massachusetts. Albany is the entry point from the west, either along the historic Mohawk Trail or the Massachusetts Turnpike to the south. and, of course, New York City, Hartford and New Haven are located to the South. The region is an important destination for tourists and history buffs.